University Chemistry ›› 2022, Vol. 37 ›› Issue (5): 2111018.doi: 10.3866/PKU.DXHX202111018

Special Issue: 第2届全国大学生化学实验创新设计竞赛

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One-Pot, Three-Step Synthesis of o-Aminophenol Derivatives from Nitro Arenes

Chengbo Sun, Zhubao Zhang, Yizhong Chen, Yuhao Kuang, Xiaojian Liao(), Pengju Feng()   

  • Received:2021-11-08 Accepted:2021-11-10 Published:2022-03-30
  • Contact: Xiaojian Liao,Pengju Feng E-mail:tliaoxj@jnu.edu.cn;pfeng@jnu.edu.cn

Abstract:

The selective reduction of nitro groups, selective protection of hydroxylamine, and the [3, 3]-σ rearrangement are fundamental reactions in organic chemistry. This experiment systematically incorporates three basic reactions into a compact, one-pot chemical transformation in 3.5 h. The reaction occurs abundantly, and can be easily monitored by thin-layer chromatography. High value-added functionalized o-aminophenol derivatives could be obtained from simple nitro arenes in one pot. In addition, the three-step reaction can be run separately with high yields. The final product can be purified using silica gel column chromatography, and the structure can be determined via high-resolution mass spectrometry and nuclear magnetic resonance spectroscopy. This reaction is based on fundamental organic chemistry concepts. It is important for undergraduates to learn functional group transformations and develop the ability to observe various experimental phenomena. Moreover, the reaction has high efficiency in a short time and may have a wide range of applications in the preparation of functional o-aminophenol derivatives.

Key words: One-pot procedure, Selective reduction, Protection of hydroxylamine, [3, 3]-σ Rearrangement, o-Aminophenol

MSC2000: 

  • G64